Chloroquine (antimalaria medication with anti SARS-CoV activity) solubility in supercritical carbon dioxide

Mahboubeh Pishnamazi; Saber Hosseini; Samyar Zabihi; Fatemeh Borousan; Ali Zeinolabedini Hezave; Azam Marjani; Saeed Shirazian

doi:10.1016/j.molliq.2020.114539

Chloroquine (antimalaria medication with anti SARS-CoV activity) solubility in supercritical carbon dioxide

J Mol Liq. 2021 Jan 15:322:114539. doi: 10.1016/j.molliq.2020.114539. Epub 2020 Oct 13.

Authors

Mahboubeh Pishnamazi^{1

2}, Saber Hosseini³, Samyar Zabihi⁴, Fatemeh Borousan^{5

6

7}, Ali Zeinolabedini Hezave^{6

7}, Azam Marjani^{8

9}, Saeed Shirazian^{10

11}

Affiliations

¹ Institute of Research and Development, Duy Tan University, Da Nang 550000, Viet Nam.
² The Faculty of Pharmacy, Duy Tan University, Da Nang 550000, Viet Nam.
³ Faculty of Chemistry, University of Semnan, Semnan, Iran.
⁴ Department of Process Engineering, Research and Development Department, Shazand-Arak Oil Refinery Company, Arak, Iran.
⁵ Department of Chemistry, Yasouj University, Yasouj 75914-353, Iran.
⁶ Incubation Centre of Arak Science and Technology Park, Fanavari Atiyeh Pouyandegan Exir Company, Arak 381314-3553, Iran.
⁷ Incubation Centre of Arak Science and Technology Park, Fanavari Arena Exir Sabz Company, Arak 381314-3553, Iran.
⁸ Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City, Viet Nam.
⁹ Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Viet Nam.
¹⁰ Department of Chemical Sciences, Bernal Institute, University of Limerick, Limerick, Ireland.
¹¹ Laboratory of Computational Modeling of Drugs, South Ural State University, 76 Lenin prospekt, 454080 Chelyabinsk, Russia.

Abstract

Unfortunately, malaria still remains a major problem in tropical areas, and it takes thousands of lives each year and causes millions of infected cases. Besides, on December 2019, a new virus known as coronavirus appeared, that its rapid prevalence caused the World Health Organization (WHO) to consider it a pandemic. As a potential drug for controlling or treating these two undesired diseases at the cellular level, chloroquine and its derivatives are being investigated, although they possess side effects, which must be reduced for effective and safe treatments. With respect to the importance of this medicine, the current research aimed to calculate the solubility of chloroquine in supercritical carbon dioxide, and evaluated effect of pressure and temperature on the solubility. The pressure varied between 120 and 400 bar, and temperatures between 308 and 338 K were set for the measurements. The experimental results revealed that the solubility of chloroquine lies between 1.64 × 10^-5 to 8.92 × 10^-4 (mole fraction) with different functionality to temperature and pressure. Although the solubility was indicated to be strong function of pressure and temperature, the effect of temperature was more profound and complicated. A crossover pressure point was found in the solubility measurements, which indicated similar behaviour to an inflection point. For the pressures higher than the crossover point, the temperature indicated direct effect on the solubility of chloroquine. On the other hand, for pressures less than the crossover point, temperature enhancement led to a reduction in the solubility of chloroquine. Moreover, the obtained solubility results were correlated via semi-empirical density-based thermodynamic correlations. Five correlations were studied including: Kumar & Johnston, Mendez-Santiago-Teja, Chrastil, Bartle et al., and Garlapati & Madras. The best performance was obtained for Mendez-Santiago-Teja's correlation in terms of average absolute relative deviation percent (12.0%), while the other examined models showed almost the same performance for prediction of chloroquine solubility.

Keywords: Chloroquine; Crossover pressure; Pharmaceuticals; Solubility; Thermodynamics.